##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-N'-[4-(2,4-Dichlorobenzyloxy)-3-methoxybenzylidene]-2-methoxybenzohydrazide
sesquihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H20 Cl2 N2 O4, 1.5(H2 O)'
_chemical_formula_sum     'C23 H23 Cl2 N2 O5.5'
_chemical_formula_iupac     'C23 H20 Cl2 N2 O4, 1.5H2 O'
_chemical_formula_weight     486.34
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.7689(16)
_cell_length_b     8.3390(17)
_cell_length_c     18.345(4)
_cell_angle_alpha     80.93(3)
_cell_angle_beta     77.85(3)
_cell_angle_gamma     86.50(3)
_cell_volume     1146.9(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1784
_cell_measurement_theta_min     2.30
_cell_measurement_theta_max     25.59
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.408
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     506
_exptl_absorpt_coefficient_mu     0.326
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.902
_exptl_absorpt_correction_T_max     0.943
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5880
_diffrn_reflns_av_R_equivalents     0.0217
_diffrn_reflns_av_sigmaI/netI     0.0476
_diffrn_reflns_theta_min     1.15
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4015
_reflns_number_gt     2630
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0846
_refine_ls_R_factor_gt     0.0485
_refine_ls_wR_factor_gt     0.1096
_refine_ls_wR_factor_ref     0.1295
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.019
_refine_ls_number_reflns     4015
_refine_ls_number_parameters     295
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0509P)²+0.5064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.449
_refine_diff_density_min     -0.331
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003)
;
_computing_publication_material     'SHELXTL (Sheldrick, 1997b)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 -0.13680(11) 0.79097(10) 0.38426(5) 0.0694(3) Uani d . 1 . .
    Cl Cl2 -0.39945(15) 0.19415(15) 0.47328(6) 0.1037(4) Uani d . 1 . .
    N N27 0.5507(3) 0.2392(3) 0.01833(11) 0.0398(5) Uani d . 1 . .
    N N17 0.5335(3) 0.1920(3) -0.04870(11) 0.0408(5) Uani d . 1 . .
    H H17 0.4404 0.2209 -0.0663 0.049 Uiso calc R 1 . .
    O O21 0.3807(2) 0.5372(2) 0.32719(10) 0.0482(5) Uani d . 1 . .
    O O22 0.6607(2) 0.3832(3) 0.27045(10) 0.0555(5) Uani d . 1 . .
    O O17 0.7940(3) 0.0557(3) -0.06310(11) 0.0590(6) Uani d . 1 . .
    O O12 0.3475(2) 0.1888(2) -0.15247(11) 0.0555(5) Uani d . 1 . .
    C C24 0.4146(3) 0.3881(3) 0.11807(13) 0.0367(6) Uani d . 1 . .
    C C22 0.5358(3) 0.4077(3) 0.22718(14) 0.0385(6) Uani d . 1 . .
    C C11 0.6317(3) 0.0618(3) -0.16009(14) 0.0368(6) Uani d . 1 . .
    C C26 0.2499(3) 0.5272(3) 0.21774(14) 0.0401(6) Uani d . 1 . .
    H H26 0.1491 0.5849 0.2375 0.048 Uiso calc R 1 . .
    C C25 0.2655(3) 0.4755(3) 0.14804(14) 0.0408(6) Uani d . 1 . .
    H H25 0.1755 0.4996 0.1213 0.049 Uiso calc R 1 . .
    C C17 0.6597(3) 0.1018(3) -0.08664(14) 0.0391(6) Uani d . 1 . .
    C C21 0.3828(3) 0.4934(3) 0.25773(14) 0.0385(6) Uani d . 1 . .
    C C12 0.4826(3) 0.1046(3) -0.19211(15) 0.0406(6) Uani d . 1 . .
    C C23 0.5507(3) 0.3560(3) 0.15837(14) 0.0384(6) Uani d . 1 . .
    H H23 0.6519 0.2992 0.1384 0.046 Uiso calc R 1 . .
    C C27 0.4222(3) 0.3281(3) 0.04695(14) 0.0398(6) Uani d . 1 . .
    H H27 0.3304 0.3555 0.0215 0.048 Uiso calc R 1 . .
    C C13 0.4770(4) 0.0628(3) -0.26198(16) 0.0495(7) Uani d . 1 . .
    H H13 0.3790 0.0927 -0.2832 0.059 Uiso calc R 1 . .
    C C31 0.0713(4) 0.5174(3) 0.39109(14) 0.0424(7) Uani d . 1 . .
    C C16 0.7684(3) -0.0254(3) -0.20037(15) 0.0434(7) Uani d . 1 . .
    H H16 0.8676 -0.0564 -0.1801 0.052 Uiso calc R 1 . .
    C C14 0.6156(4) -0.0228(4) -0.30015(16) 0.0532(8) Uani d . 1 . .
    H H14 0.6103 -0.0505 -0.3468 0.064 Uiso calc R 1 . .
    C C37 0.2280(4) 0.6251(3) 0.36038(15) 0.0472(7) Uani d . 1 . .
    H H37A 0.1978 0.7116 0.3228 0.057 Uiso calc R 1 . .
    H H37B 0.2547 0.6746 0.4010 0.057 Uiso calc R 1 . .
    C C15 0.7606(4) -0.0670(3) -0.26974(16) 0.0517(8) Uani d . 1 . .
    H H15 0.8537 -0.1248 -0.2955 0.062 Uiso calc R 1 . .
    C C32 -0.1006(4) 0.5803(4) 0.40135(14) 0.0469(7) Uani d . 1 . .
    C C36 0.0922(4) 0.3508(4) 0.40978(15) 0.0525(8) Uani d . 1 . .
    H H36 0.2054 0.3046 0.4045 0.063 Uiso calc R 1 . .
    C C33 -0.2460(4) 0.4836(4) 0.42571(16) 0.0584(8) Uani d . 1 . .
    H H33 -0.3596 0.5288 0.4305 0.070 Uiso calc R 1 . .
    C C34 -0.2185(5) 0.3197(5) 0.44249(16) 0.0617(9) Uani d . 1 . .
    C C22A 0.8218(4) 0.3038(4) 0.24026(19) 0.0682(10) Uani d . 1 . .
    H H22A 0.7993 0.1941 0.2360 0.102 Uiso calc R 1 . .
    H H22B 0.9031 0.3032 0.2731 0.102 Uiso calc R 1 . .
    H H22C 0.8713 0.3607 0.1913 0.102 Uiso calc R 1 . .
    C C35 -0.0504(5) 0.2514(4) 0.43596(16) 0.0621(9) Uani d . 1 . .
    H H35 -0.0336 0.1400 0.4490 0.074 Uiso calc R 1 . .
    C C12A 0.1899(4) 0.2271(4) -0.1805(2) 0.0722(10) Uani d . 1 . .
    H H12A 0.2160 0.2976 -0.2278 0.108 Uiso calc R 1 . .
    H H12B 0.1063 0.2805 -0.1450 0.108 Uiso calc R 1 . .
    H H12C 0.1411 0.1289 -0.1874 0.108 Uiso calc R 1 . .
    O O1 0.9358(4) 0.1894(3) 0.05343(18) 0.1153(11) Uani d D 1 . .
    H H1A 0.8732 0.1775 0.0217 0.138 Uiso d RD 1 . .
    H H1B 1.0302 0.1305 0.0513 0.138 Uiso d RD 1 . .
    O O2 0.0665(6) 0.4574(6) 0.9588(3) 0.0901(15) Uiso d PD 0.50 . .
    H H2A 0.0498 0.5567 0.9654 0.108 Uiso d PRD 0.50 . .
    H H2B 0.0095 0.3882 0.9929 0.108 Uiso d PRD 0.50 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C32 . 1.751(3) ?
    Cl2 C34 . 1.747(3) ?
    N27 C27 . 1.279(3) ?
    N27 N17 . 1.383(3) ?
    N17 C17 . 1.341(3) ?
    N17 H17 . 0.8600 ?
    O21 C21 . 1.377(3) ?
    O21 C37 . 1.431(3) ?
    O22 C22 . 1.365(3) ?
    O22 C22A . 1.426(3) ?
    O17 C17 . 1.229(3) ?
    O12 C12 . 1.369(3) ?
    O12 C12A . 1.425(3) ?
    C24 C25 . 1.389(3) ?
    C24 C23 . 1.403(3) ?
    C24 C27 . 1.458(3) ?
    C22 C23 . 1.377(3) ?
    C22 C21 . 1.407(3) ?
    C11 C16 . 1.396(3) ?
    C11 C12 . 1.409(4) ?
    C11 C17 . 1.499(4) ?
    C26 C21 . 1.379(4) ?
    C26 C25 . 1.392(4) ?
    C26 H26 . 0.9300 ?
    C25 H25 . 0.9300 ?
    C12 C13 . 1.390(4) ?
    C23 H23 . 0.9300 ?
    C27 H27 . 0.9300 ?
    C13 C14 . 1.380(4) ?
    C13 H13 . 0.9300 ?
    C31 C36 . 1.386(4) ?
    C31 C32 . 1.391(4) ?
    C31 C37 . 1.513(4) ?
    C16 C15 . 1.385(4) ?
    C16 H16 . 0.9300 ?
    C14 C15 . 1.365(4) ?
    C14 H14 . 0.9300 ?
    C37 H37A . 0.9700 ?
    C37 H37B . 0.9700 ?
    C15 H15 . 0.9300 ?
    C32 C33 . 1.383(4) ?
    C36 C35 . 1.382(4) ?
    C36 H36 . 0.9300 ?
    C33 C34 . 1.367(5) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.381(5) ?
    C22A H22A . 0.9600 ?
    C22A H22B . 0.9600 ?
    C22A H22C . 0.9600 ?
    C35 H35 . 0.9300 ?
    C12A H12A . 0.9600 ?
    C12A H12B . 0.9600 ?
    C12A H12C . 0.9600 ?
    O1 H1A . 0.8532 ?
    O1 H1B . 0.8547 ?
    O2 H2A . 0.8539 ?
    O2 H2B . 0.8485 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C27 N27 N17 . . 114.0(2) ?
    C17 N17 N27 . . 121.1(2) ?
    C17 N17 H17 . . 119.5 ?
    N27 N17 H17 . . 119.5 ?
    C21 O21 C37 . . 117.1(2) ?
    C22 O22 C22A . . 117.1(2) ?
    C12 O12 C12A . . 119.8(2) ?
    C25 C24 C23 . . 118.9(2) ?
    C25 C24 C27 . . 118.9(2) ?
    C23 C24 C27 . . 122.1(2) ?
    O22 C22 C23 . . 125.1(2) ?
    O22 C22 C21 . . 115.0(2) ?
    C23 C22 C21 . . 119.9(2) ?
    C16 C11 C12 . . 117.5(2) ?
    C16 C11 C17 . . 116.1(2) ?
    C12 C11 C17 . . 126.4(2) ?
    C21 C26 C25 . . 120.4(2) ?
    C21 C26 H26 . . 119.8 ?
    C25 C26 H26 . . 119.8 ?
    C24 C25 C26 . . 120.5(2) ?
    C24 C25 H25 . . 119.8 ?
    C26 C25 H25 . . 119.8 ?
    O17 C17 N17 . . 121.8(2) ?
    O17 C17 C11 . . 121.2(2) ?
    N17 C17 C11 . . 117.1(2) ?
    O21 C21 C26 . . 125.3(2) ?
    O21 C21 C22 . . 115.1(2) ?
    C26 C21 C22 . . 119.5(2) ?
    O12 C12 C13 . . 122.3(2) ?
    O12 C12 C11 . . 117.6(2) ?
    C13 C12 C11 . . 120.0(2) ?
    C22 C23 C24 . . 120.7(2) ?
    C22 C23 H23 . . 119.7 ?
    C24 C23 H23 . . 119.7 ?
    N27 C27 C24 . . 122.2(2) ?
    N27 C27 H27 . . 118.9 ?
    C24 C27 H27 . . 118.9 ?
    C14 C13 C12 . . 120.6(3) ?
    C14 C13 H13 . . 119.7 ?
    C12 C13 H13 . . 119.7 ?
    C36 C31 C32 . . 116.7(3) ?
    C36 C31 C37 . . 121.6(3) ?
    C32 C31 C37 . . 121.8(3) ?
    C15 C16 C11 . . 121.8(3) ?
    C15 C16 H16 . . 119.1 ?
    C11 C16 H16 . . 119.1 ?
    C15 C14 C13 . . 120.3(3) ?
    C15 C14 H14 . . 119.9 ?
    C13 C14 H14 . . 119.9 ?
    O21 C37 C31 . . 112.3(2) ?
    O21 C37 H37A . . 109.1 ?
    C31 C37 H37A . . 109.1 ?
    O21 C37 H37B . . 109.1 ?
    C31 C37 H37B . . 109.1 ?
    H37A C37 H37B . . 107.9 ?
    C14 C15 C16 . . 119.8(3) ?
    C14 C15 H15 . . 120.1 ?
    C16 C15 H15 . . 120.1 ?
    C33 C32 C31 . . 122.8(3) ?
    C33 C32 Cl1 . . 118.0(2) ?
    C31 C32 Cl1 . . 119.2(2) ?
    C35 C36 C31 . . 121.8(3) ?
    C35 C36 H36 . . 119.1 ?
    C31 C36 H36 . . 119.1 ?
    C34 C33 C32 . . 118.2(3) ?
    C34 C33 H33 . . 120.9 ?
    C32 C33 H33 . . 120.9 ?
    C33 C34 C35 . . 121.4(3) ?
    C33 C34 Cl2 . . 119.3(3) ?
    C35 C34 Cl2 . . 119.3(3) ?
    O22 C22A H22A . . 109.5 ?
    O22 C22A H22B . . 109.5 ?
    H22A C22A H22B . . 109.5 ?
    O22 C22A H22C . . 109.5 ?
    H22A C22A H22C . . 109.5 ?
    H22B C22A H22C . . 109.5 ?
    C34 C35 C36 . . 119.1(3) ?
    C34 C35 H35 . . 120.5 ?
    C36 C35 H35 . . 120.5 ?
    O12 C12A H12A . . 109.5 ?
    O12 C12A H12B . . 109.5 ?
    H12A C12A H12B . . 109.5 ?
    O12 C12A H12C . . 109.5 ?
    H12A C12A H12C . . 109.5 ?
    H12B C12A H12C . . 109.5 ?
    H1A O1 H1B . . 115.6 ?
    H2A O2 H2B . . 116.3 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O1 H1B O17 2_755 0.85 2.02 2.852(3) 164 yes
    O2 H2A O1 2_666 0.85 2.10 2.918(6) 161 yes
    O2 H2B O1 1_456 0.85 1.89 2.711(6) 162 yes
    O1 H1A O17 . 0.85 2.19 2.987(3) 155 yes
    O1 H1A N27 . 0.85 2.54 3.180(3) 133 yes
    N17 H17 O12 . 0.86 1.93 2.625(3) 137 yes
data_global
_journal_date_recd_electronic     2007-10-16
_journal_date_accepted     2007-10-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     11
_journal_page_first     o4396
_journal_page_last     o4396
_journal_paper_category     QO
_journal_coeditor_code     HB2588
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    'Liu, Shou-Xin'
;
College of Chemical & Pharmaceutical Engineering
Hebei University of Science & Technology
Shijiazhuang 050018
People's Republic of China
;
_publ_contact_author_email     liu_shouxin@163.com
_publ_contact_author_fax     '086(0311)87828831'
_publ_contact_author_phone     '086(0311)96707094'
_publ_section_title
;\
(E)-N'-[4-(2,4-Dichlorobenzyloxy)-3-methoxybenzylidene]-2-\
methoxybenzohydrazide sesquihydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Liu, Shou-Xin' .
;
College of Chemical & Pharmaceutical Engineering
Hebei University of Science & Technology
Shijiazhuang 050018
People's Republic of China
;
    "Tian, Xia" .
;
College of Sciences
Hebei University of Science & Technology
Shijiazhuang 050018
People's Republic of China
;
    "Zhen, Xiao-Li" .
;
College of Sciences
Hebei University of Science & Technology
Shijiazhuang 050018
People's Republic of China
;
    "Li, Zhen-Chao" .
;
College of Sciences
Hebei University of Science & Technology
Shijiazhuang 050018
People's Republic of China
;
    "Han, Jian-Rong"
;
Additional contact author, email: han_jianrong@163.com.
;
;
College of Sciences
Hebei University of Science & Technology
Shijiazhuang 050018
People's Republic of China
;
